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WO2018142101A1 - Compositions pharmaceutiques et de nettoyage et leur utilisation en traitement - Google Patents

Compositions pharmaceutiques et de nettoyage et leur utilisation en traitement Download PDF

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Publication number
WO2018142101A1
WO2018142101A1 PCT/GB2018/050104 GB2018050104W WO2018142101A1 WO 2018142101 A1 WO2018142101 A1 WO 2018142101A1 GB 2018050104 W GB2018050104 W GB 2018050104W WO 2018142101 A1 WO2018142101 A1 WO 2018142101A1
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WO
WIPO (PCT)
Prior art keywords
methyl carbonate
methoxycarbonyl methyl
wound
dmdc
pharmaceutical composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB2018/050104
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English (en)
Inventor
Jerome VAUGHAN
Gregg Hill
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vornagain Ltd
Biovorn Ltd
Original Assignee
Vornagain Ltd
Biovorn Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Publication of WO2018142101A1 publication Critical patent/WO2018142101A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/225—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics

Definitions

  • the present invention relates to pharmaceutical, sterilizing and cleaning compositions comprising methoxycarbonyl methyl carbonate; methoxycarbonyl methyl carbonate for use in the treatment of humans and non-human animals; methods of medical treatment using methoxycarbonyl methyl carbonate; and sterilisation and cleaning methods using methoxycarbonyl methyl carbonate.
  • the epidermis (outermost layer) and dermis (inner layer) of the skin forms a protective barrier against the external environment.
  • the normal wound healing process can be broadly classified into three stages. The first stage is the inflammatory phase which lasts between zero and two days and involves an orderly recruitment of cells to the wound area. This inflammatory phase is followed by the second phase, the proliferative phase, which lasts between two and seven days. During the proliferative phase, fibroblasts, keratinocytes and other cells in the wound begin to proliferate and close the wound.
  • the third phase of wound healing is the maturation phase which may last up to three weeks, at the end of which the wound should be completely healed due to restructuring of the initial scar tissue.
  • the wound does not follow this normal process, due to a number of factors.
  • the wound is infected with bacterial, fungal or viral pathogens which prevent or reduce the speed of wound healing or otherwise flare up or reopen wounds that have seemingly healed.
  • Many stalled wounds including those which refuse to heal due to an underlying fungal, viral or bacterial infection, can be treated with known anti-infective agents.
  • many such anti-infective agents are relatively expensive and/or are now suffering from drug resistance in the relevant bacteria, fungus or virus.
  • many anti-infective agents are not able to be applied topically to an infected wound, and must be ingested by the patient; or may only be used under specific clinical circumstances.
  • anti-infective agents including antiseptic and antibiotic agents are effective against only a single organism or a small range of organisms, and therefore can only be utilised on specific wounds which include the relevant underlying pathogen.
  • the identification of specific pathogens and the careful selection of an effective anti- infective agent can be time consuming.
  • mastitis which can be caused by many different types of bacteria
  • treatment by means of antibiotics is normally quite effective.
  • this method of treatment of such infectious conditions has a major drawback of rendering an animal's milk unsuitable for consumption.
  • Antibiotic treatment of mastitis results in milk which cannot be used for a long period of time after treatment is finished, until residual antibiotic compounds are substantially undetectable in the milk.
  • wounds on animals these can be very difficult to treat even with current wound healing compositions, due to further dirt and infective agents entering the wound during wound healing, as the animal goes about its day to day routine.
  • Many anti-infective agents applied to animal wounds are in the form of aqueous compositions which are easily removed from the wound site under normal environmental conditions under which the animal lives.
  • compositions for use with human or non-human mammal patients, for the treatment of infectious disease, wounds or skin conditions which overcomes or mitigates at least one of the above mentioned problems. It would also be advantageous to provide a pharmaceutical composition for a human or non-human mammal patient which comprises an agent capable of enhancing wound healing per se and/or having anti-bacterial, anti-fungal and/or anti-viral properties.
  • compositions which may be used as an anti-infective agent on human or non-human mammal patients, but which also can be used as a sterilising or cleaning agent for hard or soft surfaces.
  • anti-microbial compositions cannot be used in wound dressings such as gauzes, bandages and plasters due to their inherent instability or likelihood of environmental break down of the composition during the time period in which the dressing is applied to a patient, especially in the case of animal patients. It would therefore also be advantageous to provide a pharmaceutical composition which can be used in a topical application per se, but which can also be used on or in a wound dressing for indications which require contact of the pharmaceutical composition for relatively longer periods of time.
  • a pharmaceutical composition comprising methoxycarbonyl methyl carbonate, and a pharmaceutically acceptable carrier or diluent.
  • Methoxycarbonyl methyl carbonate is also known as dimethyl dicarbonate and has the chemical formula H3C-O-CO-O-CO-O-CH3 and will hereinafter be referred to as "DMDC”.
  • the pharmaceutical composition may be in a topical administration format.
  • the pharmaceutical composition may be a topically administrable pharmaceutical composition.
  • a pharmaceutical composition comprising methoxycarbonyl methyl carbonate and a pharmaceutically acceptable carrier or diluent, for use in the treatment or prevention of a skin disease or condition, wherein the pharmaceutical composition is applied by topical administration.
  • topical administration relates to the application of a substance to a body surface, such as skin.
  • the topical administration is epicutaneous (directly onto the surface of the skin), otherwise known as "dermal administration”.
  • the pharmaceutical compositions of the first and second aspects of the invention may be used to treat humans or non-human animals, especially non-human mammals. Suitable non-human mammals include sheep, goats, cows, pigs, dogs, cats and horses, for example.
  • the DMDC may be present in the pharmaceutical composition of the first or second aspects of the invention in a concentration of at least 0.01% wt, at least 0.05% wt, at least 0.1 % wt, at least 0.2% wt, at least 0.3% wt, at least 0.4% wt, at least 0.5% wt, at least 0.6% wt, at least 0.7% wt, at least 0.8% wt, at least 0.9% wt, or at least 1.0% wt.
  • the DMDC may be present in the pharmaceutical composition in an amount of no more than 99% wt, no more than 90% wt, no more than 80% wt, no more than 70% wt, no more than 60% wt, no more than 50% wt, no more than 40% wt, no more than 30% wt, no more than 20% wt, no more than 10% wt, no more than 9% wt, no more than 8% wt, no more than 7% wt, no more than 6% wt or no more than 5% wt.
  • the DMDC is present in the pharmaceutical composition in an amount of between 0.05% wt and 10 % wt, 0.5% wt and 7.5% wt, 0.75% wt and 6.5% wt or between 1% wt and 5% wt.
  • the pharmaceutical composition may comprise a topically administrable composition comprising between 0.5% wt and 10% wt DMDC.
  • the pharmaceutical composition may be provided in any suitable form for topical administration, including, but not limited to, ointments, gels, creams, lotions, foams, sprays, mousses, patches, powders, pastes, hydrogels, emulsions (including oil- in-water, water-in-oil, oil-in-water-in-oil, water-in-oil-in-water emulsions) or any combination thereof.
  • the pharmaceutical composition is provided as a cream, ointment, lotion or gel, most preferably a cream or ointment.
  • the carrier or diluent preferably comprises a hydrophobic carrier or diluent selected from an oil or fat, a natural wax, a petroleum wax, a hydrocarbon, or any suitable mixture thereof.
  • the carrier or diluent may comprise an organic solvent.
  • Suitable natural waxes include beeswax (including white or yellow beeswax), a carnauba wax, a wool wax, a lanolin (such as purified lanolin or anhydrous lanolin) or any suitable combination thereof.
  • Suitable petroleum waxes include hard paraffin and microcrystalline wax.
  • Suitable hydrocarbons include liquid paraffin, soft paraffin (including white or yellow soft paraffin), white petrolatum, yellow petrolatum or any suitable combination thereof.
  • the pharmaceutical composition may comprise any other suitable fat or oil base as a carrier or diluent, such as those described in the British Pharmacopoeia, 2017 Edition or the European Pharmacopoeia, 9 th Edition.
  • Suitable organic solvents include, but are not limited to, non-polar solvents, polar aprotic solvents and polar protic solvents.
  • Suitable non-polar solvents include alkanes (such as hexane and pentane), cycloalkanes (such as cyclopentane and cyclohexane), benzene, toluene, chloroform, diethylether and dichloromethane.
  • Suitable polar aprotic solvents include tetrahydrofuran, ethyl acetate, acetone, dimethylformamide, acetonitrile, dimethyl sulphoxide and propylene carbonate.
  • Polar protic solvents include, but are not limited to alcohols (such as methanol, ethanol, propanol, isopropanol and butanol, for example), formic acid and acetic acid.
  • an organic solvent as defined above is particularly useful for pharmaceutical compositions in the form of sprays, for example. Sprays may be used to ensure hard to reach areas of skin are coated with the pharmaceutical compositions, e.g. between hooves or under skin folds.
  • the DMDC may be encapsulated. In some embodiments the DMDC may be incorporated into liposomes.
  • the pharmaceutical compositions of the invention may comprise an aqueous carrier, including water per se.
  • the DMDC may be microencapsulated. Suitable encapsulants for encapsulation or micro-encapsulation include yeast cells, exine shell materials (such as from pollen grains) and the like, for example.
  • the carrier or diluent may be an aqueous carrier or diluent, which may comprise water per se, such as de-ionised water, for example.
  • the pharmaceutical composition of the invention may further comprise one or more pharmaceutical excipients. Suitable pharmaceutical excipients include, but are not limited to, emulsifiers, surfactants, solvents, co-solvents, preservatives, stabilisers, buffers, solubilizers, dispersal agents, anti-oxidants, thickeners, softeners, lubricants, emollients, and one or more further skin healing or conditioning agents.
  • Suitable preservatives include those selected from the list comprising: a quaternary ammonium compound such as e.g. benzalkonium chloride (N-benzyl-N- (C8-C18-alkyl)-N,N-dimethylammonium chloride), benzoxonium chloride, benzethonium chloride, cetrimide (hexadecyl-trimethylammonium bromide), sepazonium chloride, cetylpyridinium chloride, domiphen bromide or the like; quaternized ammonium cyclodextrin compounds (QACD compounds as described, for instance, in US 3,453,257 or US 5,241,059; alkyl-mercury salts of thiosalicyclic acid, such as e.g.
  • a quaternary ammonium compound such as e.g. benzalkonium chloride (N-benzyl-N- (C8-C18-alkyl)-N,
  • thiomersal phenylmercuric nitrate, phenylmercuric acetate or phenylmercuric borate
  • parabens such as e.g. methylparaben or propylparaben
  • alcohols such as e.g. chlorobutanol, benzyl alcohol or phenyl ethyl alcohol
  • biguanide derivatives such as e.g.
  • chlorohexidine or polyhexamethylene biguanide sodium perborate ; imidazolidinyl urea; sorbic acid; stabilized oxychloro complexes; polyglycol-polyamine condensation resins; stabilized hydrogen peroxide generated from a source of hydrogen peroxide for providing an effective trace amount of resultant hydrogen peroxide, e.g. sodium perborate tetrahydrate; and/or any suitable combination thereof.
  • Preferred preservatives are quaternary ammonium compounds, in particular benzalkonium chloride, cetrimide and phenyl ethyl alcohol. Where appropriate, a sufficient amount of preservative is added to the pharmaceutical composition to ensure protection against secondary contaminations during use.
  • Suitable surfactants or emulsifiers include, but are not limited to, non-ionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants and zwitterionic surfactants.
  • Suitable cationic surfactants include quaternary ammonium salts, for example.
  • Suitable anionic surfactants include carboxylates, such as sodium or potassium salts of a fatty acid; and sulphates of fatty acids salts, such as sodium laureth sulphate and sodium dodecyl sulphate, for example.
  • Suitable non-ionic surfactants include, but are not limited to ethers of fatty alcohols, polyol esters, polyoxyethylene esters, polyoxamers or the like.
  • Suitable polyoxyethylene esters include, but are not limited to polyethylene glycol (PEG).
  • Suitable polyol esters include, but are not limited to glycol and glycerol esters, and sorbitan derivatives.
  • compositions of the invention for topical application should not contain ingredients that may cause irritation to the skin, even on prolonged use. Compounds to which sensitization may occur should be avoided. Thus, balanced amphoteric surfactants may be preferred as the surfactant.
  • amphoteric surfactant is well known to those skilled in the art. Such surfactants (which may also be known as ampholytic surfactants) possess at least one anionic group and at least one cationic group, and can therefore have anionic, non-ionic or cationic properties depending on the pH. If the isoelectric point of the molecule occurs at pH7, the molecule is said to be balanced. Amphoteric surfactants may have detergent and disinfectant properties. Balanced amphoteric surfactants may be particularly non-irritant to the skin and therefore preferred in topical pharmaceutical compositions of the invention. Suitable amphoteric surfactants include aminocarboxylic acids, aminopropionic acid derivatives, imidazoline derivatives, dodicin, pendecamaine or long-chain betaines, or cocamidopropyl betaines.
  • Suitable complexing agents include, but are not limited to those selected from: disodium-ethylenediamine tetraacetate, ethylenediamine tetraacetic acid (EDTA); chelating agents having phosphonic acid or phosphonate groups, preferably organophosphonates, particularly amino tri(lower alkylene phosphonic acids) or the like; cyclodextrins, e.g. ⁇ -, ⁇ - or ⁇ -cyclodextrin, e.g.
  • compositions of the present invention may further comprise antioxidants such as ascorbic acid, acetylcysteine, cysteine, sodium hydrogen sulphite, butylated hydroxyanisole, butylated hydroxytoluene or natural or synthetic Vitamin E derivatives, such as alpha-tocopherol or alpha-tocopherol acetate, for example.
  • antioxidants such as ascorbic acid, acetylcysteine, cysteine, sodium hydrogen sulphite, butylated hydroxyanisole, butylated hydroxytoluene or natural or synthetic Vitamin E derivatives, such as alpha-tocopherol or alpha-tocopherol acetate, for example.
  • compositions of the present invention may further comprise stabilizers such thiourea, thiosorbitol, sodium dioctyl sulphosuccinate or monothioglycerol, for example.
  • compositions of the present invention may also comprise a buffer such as acetate, ascorbate, borate, hydrogen carbonate / carbonate, citrate, gluconate, lactate, phosphate, propionate and TRIS buffers for example.
  • a buffer such as acetate, ascorbate, borate, hydrogen carbonate / carbonate, citrate, gluconate, lactate, phosphate, propionate and TRIS buffers for example.
  • the amount of a buffer added is, for example, that necessary to ensure and maintain a physiologically tolerable pH range.
  • the pH range is typically in the range of from 5 to 9, preferably from 6 to 8.5 and more preferably from 6.5 to 8.2.
  • the pharmaceutical compositions may also include one or more viscosity- increasing agents.
  • Viscosity- increasing agents include, but are not limited to polyvinylpyrrolidone, polyvinylpolypyrrolidone, methyl cellulose, hydroxypropyl cellulose (HPC), hydroxypropyl methylcellulose (HPMC), hydroxyethyl cellulose (HEC), xanthan gum, Carbopol (carbomer), and sodium hyaluronate (hyaluronic acid).
  • any particular excipient may have alternative or multiple functions, e.g. cyclodextrin or a mixture of cyclodextrins may act as two or more of a stabilizer, complexing agent and solubilizer, for example.
  • compositions of the present invention may optionally comprise one or more perfumes or colorants.
  • the pharmaceutical compositions of the invention comprise DMDC and a hydrophobic carrier.
  • the pharmaceutical compositions of the invention comprise DMDC and a carrier selected from a wax, a hydrocarbon or a mixture thereof, preferably a paraffin, petroleum jelly or a microcrystalline wax.
  • the pharmaceutical composition comprises DMDC dissolved in an organic solvent selected from methanol, ethanol, propanol, isopropanol and butanol, preferably isopropanol.
  • the pharmaceutical composition comprises a cream or ointment comprising DMDC and at least one of a paraffin, petroleum jelly and a microcrystalline wax.
  • methoxycarbonyl methyl carbonate for use in the treatment or prevention of infectious disease.
  • methoxycarbonyl methyl carbonate for use as an anti-infective agent.
  • the DMDC may be used in the third and fourth aspects of the invention per se, with no carrier or diluent, which may comprise using liquid DMDC per se (substantially 95-100% DMDC, with DMDC being liquid at ambient temperatures).
  • the DMDC may be present in a pharmaceutical composition of the first or second aspects of the invention.
  • the infectious disease may be a human infectious disease or a non-human animal infectious disease, especially a non-human mammalian infectious disease.
  • the infectious disease or infection may be a fungal disease or infection, a bacterial disease or infection, a viral disease or infection, or an oomycetic disease or infection.
  • Fungal diseases or infections suitable for treatment using the DMDC or pharmaceutical compositions of the invention include mycoses, including superficial mycoses and cutaneous mycoses, such as dermatophytosis (sometimes colloquially known as "ring worm") and non-dermatophyte mycosis.
  • Dermatophytosis is the term used to describe infections generally caused by dermatophytes, a keratinophilic ('skin loving') species of fungi. Dermatophytes against which the DMDC or pharmaceutical compositions of the invention are useful include those of genii Trichophyton, Microsporum and Epidermophyton.
  • Trichophyton species against which the DMDC or pharmaceutical compositions are useful include those from the group comprising: Trichophyton ajelloi, Trichophyton concentricum, Trichophyton equinum, Trichophyton flavescens, Trichophyton gloriae, Trichophyton megnini, Trichophyton mentagrophytes var. erinacei, Trichophyton mentagrophytes var.
  • Trichophyton onychocola Trichophyton phaseoliforme
  • Trichophyton redellii Trichophyton rubrum
  • Trichophyton rubrum downy strain Trichophyton rubrum granular strain
  • Trichophyton schoenleinii Trichophyton simii
  • Trichophyton soudanense Trichophyton terrestre
  • Trichophyton violaceum Trichophyton yaoundei.
  • Microsporum species against which the DMDC or pharmaceutical compositions are useful include those from the group comprising: Microsporum amazonicum, Microsporum audouinii, Microsporum boullardii, Microsporum canis, Microsporum canis var. distortum, Microsporum cookie, Microsporum distortum, Microsporum duboisii, Microsporum equinum, Microsporum ferrugineum, Microsporum fulvum, Microsporum gallinae, Microsporum gypseum, Microsporum langeronii, Microsporum nanum, Microsporum persicolor, Microsporum praecox, Microsporum ripariae, Microsporum rivalieri.
  • Epidermophyton species against which the DMDC or pharmaceutical compositions are useful include Epidermophyton floccosum
  • Dermophytosis diseases against which the DMDC or pharmaceutical compositions are useful include Tinea mycoses.
  • Tinea mycoses include Tinea pedis, Tinea unguuim, Tinea manuum, Tinea cruris, Tinea corporis, Tinea capitis, Tinea faciei, Tinea barbeae, Tinea inbricata, and Tinea incognito.
  • the DMDC or pharmaceutical compositions may also be used to treat non- dermatophytosis fungal diseases, such as non-dermatophyte onchomycosis, for example. Examples of non-dermatophyte onchomycosis include Tinea nigra and Tinea diversicolor, for example.
  • the fungal disease may be caused by a yeast, and which may be superficial, cutaneous or sub-cutaneous.
  • the yeast may be a yeast of the genus Candida, for example.
  • Candida species against which the DMDC or pharmaceutical compositions of the invention may be effective include, Candida albicans, Candida glabrata, Candida tropicalis, Candida lusitaniae, for example.
  • Oomycetic diseases include oomycosis, including the oomycetic diseases pythiosis and lagenidiosis. Oomycetic diseases may be caused by oomycetes of the genii Pythium, Lagenidium, Phytophthera or Diasperangium.
  • Bacterial diseases include bacterial skin infections such as dermatophilosis (such as caused by the bacteria Dermatophilus congolensis, for example, and known colloquially as “rain scald", “lumpy wool disease” or “streptotrichosis” for example); skin diseases caused by Pseudomenas aerugiosm (e.g. fleece rot in sheep); foot rot caused by, for example, Fusobacteriumnecrophorumor Bacteroides melaninogenicus; and staphylococcus dermatitis (for example, caused by bacteria of the Staphylococcus species, e.g. Staphylococcus aureus or Staphylococcus epidermis).
  • dermatophilosis such as caused by the bacteria Dermatophilus congolensis, for example, and known colloquially as "rain scald", "lumpy wool disease” or “streptotrichosis” for example
  • the DMDC or pharmaceutical compositions of the invention may be used to treat mastitis in non-human mammals.
  • the mastitis may be caused by a bacteria selected from the group comprising Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus agalactiae, Streptococcus uberis, Brucella melitensis, Corynebacterium bovis, Mycoplasma spp., Escherichia coli (E.
  • the DMDC or pharmaceutical compositions may be used to treat mastitis through intramammary infusion, for example.
  • the DMDC may be used for the prevention of infectious disease, such as those described hereinabove, or for the prevention of sexually transmitted diseases of animals, for example.
  • methoxycarbonyl methyl carbonate for use in wound healing.
  • the DMDC may be as hereinabove described and may be present in a pharmaceutical composition of the first or second aspect of the invention.
  • the wound healing may comprise cicatrisation and the use of DMDC may comprise facilitating, enhancing or speeding-up cicatrisation.
  • methoxycarbonyl methyl carbonate for use in the treatment or prevention of a dermal inflammatory disease, a dermal inflammatory condition or a non-inflammatory dermal disease or condition.
  • the DMDC may be as hereinbefore described and may be present in a pharmaceutical composition of the first or second aspect of the invention.
  • the dermal inflammatory disease or condition may be selected from the group comprising atopic dermatitis, bullous disorders, collagenoses, psoriasis, psoriatic lesions, seborrheic dermatitis or contact dermatitis, eczema, urticaria, pruritus, rosacea, prurigo nodularis, hypertrophic scarring, keloid scar formation, scleroderma, Folliculitis keloidalis nuchae, Kawasaki Disease, Sjogren-Larsson Syndrome, Grover's disease, a first degree burn, a second degree burn, a third degree burn, a fourth degree burn, cutaneous mucinosis, solar keratosis, squamous cell carcinoma or melanoma, histotic eczema, discoid eczema, hand eczema, gravitational/varicose eczema, eczematous drug eruptions,
  • a seventh aspect of the invention there is provided a method of treating or preventing an infectious disease, a wound, a dermal inflammatory disease or a dermal condition in a human or non-human mammal patient, the method comprising administration of a composition comprising methoxycarbonyl methyl carbonate to the patient in a pharmaceutically effective amount thereof.
  • the method may comprise topical administration.
  • the method may comprise administering the DMDC in a pharmaceutical composition according to the first aspect or second aspect of the invention.
  • the method may comprise administering a pharmaceutical composition of the first aspect of the invention in the form of a cream, lotion, gel, ointment, foam, spray, mousse, patch, powder, paste, or emulsion, preferably a cream or ointment.
  • the method may comprise a method of wound healing, such as a method of cicatrisation, for example.
  • a sterilising or cleaning composition comprising methoxycarbonyl methyl carbonate in a carrier or diluent.
  • the carrier or diluent may comprise a non-aqueous carrier or diluent.
  • the non-aqueous carrier may be selected from an oil, a fat, a natural wax, a petroleum wax, hydrocarbon or any suitable mixture thereof.
  • Suitable natural waxes include beeswax, carnauba wax, wool wax, lanolin or any suitable combination thereof.
  • Suitable petroleum waxes include hard paraffin and microcrystalline wax.
  • Suitable hydrocarbons include liquid paraffin, soft paraffin, white petrolatum, yellow petrolatum and any suitable combination thereof.
  • the non-aqueous carrier comprises an organic solvent.
  • Suitable organic solvents include, but are not limited to, non-polar solvents, polar aprotic solvents and polar protic solvents.
  • Suitable non-polar solvents include alkanes (such as hexane and pentane), cycloalkanes (such as cyclopentane and cyclohexane), benzene, toluene, chloroform, diethylether and dichlorome thane.
  • Suitable polar aprotic solvents include tetrahydrofuran, ethyl acetate, acetone, dimethylformamide, acetonitrile, dimethyl sulphoxide and propylene carbonate.
  • Polar protic solvents include, but are not limited to alcohols (such as methanol, ethanol, propanol, isopropanol and butanol, for example), formic acid and acetic acid.
  • the DMDC may be present in the sterilising or cleaning composition as a suspension of DMDC in the non-aqueous carrier, or a solution of DMDC in the non- aqueous carrier.
  • the carrier or diluent may be an aqueous carrier or diluent, such as water (especially de-ionised water) or a mixture of water and one or more further solvents (especially water and an alcohol, such as isopropanol).
  • aqueous carrier or diluent such as water (especially de-ionised water) or a mixture of water and one or more further solvents (especially water and an alcohol, such as isopropanol).
  • the DMDC may be encapsulated or located within liposomes and the carrier or diluent may be an aqueous carrier, including water per se.
  • the concentration of the DMDC in the carrier or diluent may be at least 0.01% wt, 0.05% wt, 0.1% wt, 0.2% wt, 0.3% wt, 0.4% wt, 0.5%, 0.75%, 1% wt, 5% wt, 10% wt, 20% wt, 30% wt, 40% wt, 50% wt, 60% wt, 70% wt, 80% wt, or at least 90% wt.
  • the DMDC may be present at a concentration of between 0.01% wt and l0% wt.
  • the sterilising or cleaning composition may further comprise one or more surfactants, which may be selected from non-ionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants or zwitter ionic surfactants.
  • the or each surfactant may be as described hereinabove for the first or second aspects of the invention.
  • the sterilising or cleaning composition may further comprise one or more bleaching agents such as hydrogen peroxide, for example, one or more anti -oxidants, one or more foaming agents, one or more colours, one or more perfumes, one or more acids, and/or one or more further anti-infective agents.
  • bleaching agents such as hydrogen peroxide, for example, one or more anti -oxidants, one or more foaming agents, one or more colours, one or more perfumes, one or more acids, and/or one or more further anti-infective agents.
  • the sterilising or cleaning composition may be in liquid or solid form.
  • the sterilising or cleaning composition may be in the form of a solid soap, a gel or a foam, for example.
  • the sterilising or cleaning composition may be a liquid and may be in the form of a spray.
  • an application device comprising a sterilising or cleaning composition of the eighth aspect of the invention.
  • the application device may comprise a pump (which may be a hand pump, a pressurised pump, a non-pressurised pump, an aerosol container or the like for example).
  • the sterilising or cleaning composition may be part of a kit comprising the sterilising or cleaning composition and a separate applicator.
  • the applicator may comprise a brush, pad, cloth or the like, for example.
  • the sterilising or cleaning composition may be coated on or present within a cleaning or sterilising article, such as a cleaning or sterilising wipe, cloth or pad, for example.
  • a method of sterilising or cleaning a surface comprising applying to said surface a composition comprising methoxycarbonyl methyl carbonate.
  • the method may comprise applying to said surface a sterilising or cleaning composition as described hereinabove for the eighth aspect of the invention.
  • the method may comprise applying the composition to the surface for a defined period of time which may be at least 1 second, 2 seconds, 3 seconds, 4 seconds, 5 seconds, 6 seconds, 7 seconds, 8 seconds, 9 seconds, 10 seconds, 15 seconds, 20 seconds, 30 seconds, 45 seconds or at least 60 seconds.
  • the method may comprise applying the composition to the surface for a time period of at least 2 minutes, 3 minutes, 4 minutes, 5 minutes, 10 minutes, 15 minutes or 30 minutes.
  • the method may comprise applying the composition to the surface in the form of a spray, foam, gel, cream, powder, liquid, mousse or emulsion, for example.
  • the method may comprise a method of sterilisation or cleaning of a hard surface.
  • the hard surface may be metal, alloy, wood, plastics, rubber, ceramic, or any combination thereof, for example.
  • the method may comprise a method of sterilisation or cleaning of an item or a piece of equipment, such as medical instruments, medical devices, patient transport devices, farming implements, milking machines, paper mill apparatus, animal dips (such as sheep dips, for example) or food production apparatus.
  • the method may comprise sterilisation or cleaning of a wall or floor, in particular, but not limited to a wall or floor of an operating theatre, medical facility, an animal holding facility (such as a barn, pen, milking shed or the like, for example) or a food production facility.
  • a wound dressing comprising a wound contact layer comprising methoxycarbonyl methyl carbonate.
  • the DMDC may be coated on a surface of the wound contact layer, or maybe incorporated within the wound contact layer (such as being entrained or infused within the wound contact layer), or a combination of both.
  • the DMDC may be present in a pharmaceutical composition as described for the first or second aspect of the invention.
  • the wound contact layer may comprise a fabric layer which may be a woven, non-woven, knitted, spacer or embroidered fabric, or maybe a composite layer comprising two or more layers selected from the aforesaid fabric materials.
  • the wound dressing may further comprise an absorbent layer for absorbing wound exudate.
  • the absorbent layer may comprise a porous or fibrous material such as a porous or fibrous fabric.
  • the porous fabric may comprise a foam which may be made of a synthetic foam material.
  • the absorbent layer may overlie the wound contact layer.
  • the wound dressing may further comprise a cover or obscuring element.
  • the wound dressing may further comprise an odour control element.
  • the wound dressing may further comprise an adhesive, located on a peripheral portion, which in use enables the wound dressing to be adhered to a wound, or to skin around a wound.
  • the wound dressing may comprise a bandage, plaster, compress or the like, for example.
  • the wound dressing may alternatively or additionally comprise a wound packing material, arranged in use to at least or completely fill a wound.
  • the wound packing material may comprise a foam, gauze, cloth or hydrofire ribbon, for example.
  • the DMDC may be entrained within the wound packing material and may be present in a pharmaceutical composition as described for the first or second aspect of the invention.
  • a wound healing system comprising a wound dressing and a wound packing material, each as described for the tenth aspect of the invention hereinabove.
  • a disinfectant composition comprising methoxycarbonyl methyl carbonate dissolved or suspended in a carrier or diluent.
  • the disinfectant composition is preferably a disinfectant solution.
  • the DMDC is preferably present in the disinfectant composition at a concentration of at least 0.01 wt, 0.05% wt, 0.75% wt, 0.1% wt, 0.5% wt, 1% wt, 5% wt, 10% wt, 20% wt, 30% wt, 40% wt, 50% wt, 60% wt, 70% wt, 80% wt or at least 90% wt.
  • the concentration may be in the range of 0.01% wt to 25% wt such as between 0.01% wt and 10% wt or between 0.05% wt and 10% wt for example.
  • the carrier or diluent may be aqueous or non-aqueous.
  • the carrier or diluent is preferably as described hereinabove for the eighth aspect of the invention, and is preferably an alcohol, such as methanol, ethanol, propanol, isopropanol or butanol, for example, or water, or a mixture of water and an alcohol.
  • the disinfectant composition may be coated on or present in a disinfecting article, such as a cloth, wipe or pad, for example, or may be in the form of a liquid suitable for spraying from a spray bottle, container or the like.
  • FIG. 1A is a photograph of a wound before treatment with a pharmaceutical composition of the invention described in Example 1;
  • Figure IB is a photograph of the wound shown in Figure 1A after four days '(96 hours) treatment with the pharmaceutical composition of the invention described in Example 1;
  • Figure 2A is a photograph of a wound in a lamb's tail before treatment with a pharmaceutical composition as described in Example 2;
  • Figure 2B is a photograph of the wound shown in Figure 2A after four days '(96 hours) treatment with the pharmaceutical composition of the invention described in Example 2;
  • Figure 3 A is a photograph of a wound and inflamed skin before treatment with a pharmaceutical composition of the invention as described in Example 3;
  • Figure 3B is a photograph of the same wound shown in Figure 3A after a 24 hour treatment with the pharmaceutical composition described in Example 3;
  • Figure 4A is a photograph of a sheep's hoof suffering from foot rot before treatment with a pharmaceutical composition as described in Example 4;
  • Figure 4B is a photograph of the same sheep' s hoof of Figure 4 A after 96 hours' treatment with the pharmaceutical composition as described in Example 4;
  • Figure 6 is a photograph of petri dishes showing the presence of bacteria in milk sample 629 taken at (from left to right) one hour, four hours and six hours after incubation.
  • the top row illustrates control samples in which no pharmaceutical composition of the invention has been added.
  • the bottom row illustrates milk samples in which a pharmaceutical composition of the invention as described in Example 5 has been added;
  • Figure 7 is a photograph of the same petri dish configuration shown in Figure 6 but illustrating milk sample 961 rather than milk sample 629, of Example 5;
  • Figure 8A is a photograph of a petri-dish showing E.coli growth on LB agar containing an absorbent dressing impregnated with 50 ⁇ of 1% wt DMDC in de- ionised water, as described in Example 7;
  • Figure 8B is a photograph of a petri-dish showing E coli growth on LB agar containing an absorbent dressing impregnated with de-ionised water alone, as described in Example 7;
  • Figure 9A is a photograph of a petri-dish showing E.coli growth on LB agar inoculated with samples taken from a plastic surface treated with 1% DMDC in de- ionised water, as described in Example 8; and Figure 9B is a photograph of a petri-dish showing E.coli growth on LB agar inoculated with samples taken from a plastic surface treated with de-ionised water alone, as described in Example 8.
  • Example 1 An experiment was undertaken to ascertain the efficacy of DMDC as a wound healing compound.
  • One Easycare sheep which had suffered a wound to its left hind quarter was treated with DMDC.
  • Treatment involved the daily application of DMDC in a Petroleum jelly compound, as follows:
  • Example 2 An experiment was undertaken to ascertain the efficacy of DMDC as a wound healing compound.
  • One Easycare sheep which had suffered a wound to its tail was treated with DMDC.
  • Treatment involved the daily application of DMDC in a petroleum jelly compound, as follows:
  • FIG. 2A shows the wound before treatment
  • Figure 2B shows the wound after 96 hours treatment, which had substantially healed.
  • FIG. 4 A shows the wound and foot rot before treatment
  • Figure 4B shows the hoof after 96 hours treatment, in which the foot rot had substantially disappeared.
  • rancid milk samples were acquired from two infected cows with mastitis and immediately frozen. They were defrosted 72 hours later and, for each sample, 2 x lOmL aliquoted into separate sterile centrifuge tubes. IOOUL of DMDC (1% v/v) was added to one of these tubes and all samples were then incubated at 37oC. Every hour for 6 hours, 20uL of each sample was spread onto nutrient agar plates (petri-dishes) using sterile techniques. Plates were incubated at 37oC for 24 hours.
  • Figure 6 illustrates the presence of bacteria in milk sample 629 taken at (from left to right) one hour, four hours and six hours after incubation.
  • the top row illustrates control samples in which no pharmaceutical composition of the invention has been added.
  • the bottom row illustrates milk samples in which a 1 % (v/v) DMDC has been added; and
  • Figure 7 is a photograph of the same petri dish configuration shown in Figure 6 but illustrating milk sample 961 rather than milk sample 629.
  • Both samples 629 and 961 contained bacteria prior to DMDC addition as shown in Figure 5 (both petri dishes). No bacteria were present in DMDC-treated samples 1 to 6 hours after treatment as shown in the bottom row of Figures 6 and 7. Bacteria were present in all non-DMDC samples and increased over time, as shown in the top row of Figures 6 and 7. This demonstrates that mastitis-causing bacteria in cow milk is destroyed by 1% (v ⁇ v) DMDC addition.
  • Example 6 A wound dressing comprising DMDC was prepared as follows:
  • a 10cm x 10cm dressing was constructed in the following laminated structure: wound contact layer - polyurethane foam infused with DMDC; absorbent layer - polyurethane foam; cover - polyamide with adhesive around its periphery.
  • the wound dressing is suitable for use in treatment of closed or open wounds, or inflammatory or infected skin conditions.
  • Absorbent pads 15mm x 10mm were removed from adhesive plasters designed for wound application, and 50 ⁇ ⁇ of a 1% DMDC (v/v) in deionised water was pipetted onto each, with the composition being rapidly absorbed.
  • the control treatment was 50 ⁇ of deionised water only.
  • the absorbent pads were placed at the centre of each plate onto the agar surface and plates were incubated overnight at 37°C.
  • Figures 8 A and 8B show plates representative of 1 % DMDC in de-ionised water and deionised water only treatments, respectively. It is shown that E.coli growth is inhibited around the absorbent pad containing DMDC (as shown by the clear corona around the pad in Figure 8A), whereas no inhibition is evident in the water-only treatment (Figure 8B). These outcomes were replicated three times for both treatments with the same results.
  • a plastic tray of 43 x 32cm was divided into two areas of 32 x 20 cm, cleaned with Teepol and rinsed thoroughly to remove residual bacteria, then dried completely in a sterile laminar flow cabinet.
  • Figures 9 A and 9B show plates representative of the 1% DMDC in de-ionised water and de-ionised water only treatments respectively. It is shown that E.coli growth is completely inhibited on surfaces treated with DMDC (as shown by the lack of bacterial growth in Figure 9A), whereas prolific growth of E.coli is shown with the water-only treatment (Figure 9B). These outcomes were replicated three times for both treatments with the same results.

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Abstract

La présente invention concerne une composition pharmaceutique comprenant du carbonate de méthyle et de méthoxycarbonyle et un excipient ou un diluant pharmaceutiquement acceptable.
PCT/GB2018/050104 2017-02-03 2018-01-16 Compositions pharmaceutiques et de nettoyage et leur utilisation en traitement Ceased WO2018142101A1 (fr)

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Application Number Priority Date Filing Date Title
GB1701765.8A GB2559369A (en) 2017-02-03 2017-02-03 Pharmaceutical and cleaning compositions and their use in treatment
GB1701765.8 2017-02-03

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WO2018142101A1 true WO2018142101A1 (fr) 2018-08-09

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1392905A (en) * 1972-02-17 1975-05-07 Pierrefitte Auby Sa Therapeutic composition for medical veterinary of cosmeto- logical use
EP0017011A1 (fr) * 1979-03-22 1980-10-15 Bayer Ag Agent microbicide et son application
WO2006048457A1 (fr) * 2004-11-05 2006-05-11 Dsm Ip Assets B.V. Probiotiques et polyphenol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006035202A1 (de) * 2006-07-29 2008-01-31 Lanxess Deutschland Gmbh Konservierungsmittel auf Basis von Carbonsäureanhydriden

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1392905A (en) * 1972-02-17 1975-05-07 Pierrefitte Auby Sa Therapeutic composition for medical veterinary of cosmeto- logical use
EP0017011A1 (fr) * 1979-03-22 1980-10-15 Bayer Ag Agent microbicide et son application
WO2006048457A1 (fr) * 2004-11-05 2006-05-11 Dsm Ip Assets B.V. Probiotiques et polyphenol

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